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首页> 外文学位 >Synthetic Strategies Towards the Synthesis of Twistacenes, Oligoacenes, Polydibenzophoshole and Pentiptycene Rotor Derivatives.
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Synthetic Strategies Towards the Synthesis of Twistacenes, Oligoacenes, Polydibenzophoshole and Pentiptycene Rotor Derivatives.

机译：合成并捻的对苯二乙炔，低聚并苯乙炔，聚二苯并膦和戊苯并噻吩转子衍生物。

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摘要

Polycyclic aromatic hydrocarbons (PAHs) are a group of widely studied organic molecules due to their interesting electronic properties. Polyacene (1), has produced the most interest from this group, both because of the synthetic challenges it poses as well as its prediction to be highly conductive. Thus far a number of oligoacene precursors have been reported in the literature, but to date no system where n is greater than six (e.g. nonacene) has been reported. We have undertaken the synthetic challenge to synthesize heptacene as well as other extended oligoacenes, including polyacene. Additionally, we have synthesized tetrabenzoheptacene (2), a twisted acene, which despite its twisted nature is quite stable and displays intereresting electronic properties.*.;The development of full color red-green-blue (RGB) displays has been hindered by the lack of stable blue polymer light emitting diodes (PLEDs). We propose the synthesis of poly(dibenzophosphole) (3) as a potential candidate for a blue PLED.*.;Organic compounds possessing aromatic groups that are linearly conjugated through acetylene linkages have also received much attention. The cylindrical symmetry of the alkyne group maintains conjugation with the adjacent phenyl groups and results in low energy barriers in the ground state. However, rotation in the excited state displays a large energy difference as a function of the angle between the aromatic groups. The twisting and planarization of these aryl-alkynyl conjugated systems ultimately results in changes in both color and emission properties. We have synthesized several p-phenylene-ethynylene pentiptycene rotor derivatives (4) to probe the effects of chromophore rotation in the ground state and in the excited state both in solution and in the solid state. By incorporating pentipycene into the rotor it provides a protecting stator and a fixed central phenylene ring. The flanking ethynylphenylene rotators allow for free rotation to study the electronic properties as a function of angle. The crystal structure shows that pentiptycene rotor 4 (R=H, R1 = OMe) packs in a way that the conjugated backbone of these rotors is aligned in a parallel manner, which is desirable for the development of novel functional materials.*.;*Please refer to dissertation for diagrams.
机译：多环芳烃（PAHs）由于其有趣的电子特性而成为一组经过广泛研究的有机分子。 Polyacene（1）引起了这一组的最大兴趣，这既是由于其带来的合成挑战，又是因为预测其具有高导电性。迄今为止，文献中已经报道了许多低茂并的前体，但是迄今为止，还没有报道其中n大于6的体系（例如壬并烯）。我们已经进行了合成挑战，以合成庚烯以及其他延伸的低聚并苯，包括多并苯。此外，我们还合成了扭曲的并苯四苯并庚并（2），尽管扭曲的并苯具有相当的稳定性，并且显示出令人感兴趣的电子性能。* .;全色红绿蓝（RGB）显示器的发展受到了阻碍。缺乏稳定的蓝色聚合物发光二极管（PLED）。我们提出了聚（二苯并磷腈）（3）的合成作为蓝色PLED的潜在选择。*。具有通过乙炔键线性共轭的芳族基团的有机化合物也受到了广泛关注。炔基的圆柱对称性与相邻的苯基保持共轭，导致基态的能垒低。然而，在激发态下的旋转显示出大的能量差，该能量差是芳族基团之间的角度的函数。这些芳基-炔基共轭体系的扭曲和平面化最终导致颜色和发射性质的变化。我们合成了几种对亚苯基-亚乙炔基戊烯并戊二烯转子衍生物（4），以研究在溶液态和固态时基态和激发态的生色团旋转的影响。通过将戊烯并入转子，可提供保护定子和固定的中心亚苯基环。侧面的乙炔基亚苯基旋转器允许自由旋转，以研究电子性能随角度的变化。晶体结构表明五茂铁转子4（R = H，R1 = OMe）的堆积方式是使这些转子的共轭骨架平行排列，这对于开发新型功能材料是理想的。请参考论文的图表。

著录项

  • 作者

    Jimenez, Miguel Angel.;

  • 作者单位

    University of California, Los Angeles.;

  • 授予单位 University of California, Los Angeles.;
  • 学科 Chemistry General.;Chemistry Organic.;Chemistry Polymer.
  • 学位 Ph.D.
  • 年度 2013
  • 页码 178 p.
  • 总页数 178
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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